Originally Posted by Fidelia
He's giving you a straight-up honest answer. He IS a guy, and he probably really DOESN'T know, and whatever you pick really WILL look good to him.
So let him off the hook on this one, and either don't ask him what he thinks about the fashion choices, or ask him for a little reassurance, to help you deal directly with the insecurity issues. I'll bet he'd be really good at that.
Are you asking "Do I look good in this?" or "Does this look good on me?"
You could always go naked.